6-{4-[3-(2,5-Dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonate → 3-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione

HRID 857096노트

반응식

HRID 857096 반응식
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[C:27](=[O:28])[CH2:26][NH:25][C:24]2=[O:29])[CH:18]=1)(=O)=O.[NH2:30][CH2:31][C@@H:32]([C:34]1[CH:45]=[CH:44][C:37]2[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=2[CH:35]=1)[OH:33]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:42][C:39]1([CH3:43])[O:38][C:37]2[CH:44]=[CH:45][C:34]([C@@H:32]([OH:33])[CH2:31][NH:30][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([N:23]4[C:27](=[O:28])[CH2:26][NH:25][C:24]4=[O:29])[CH:20]=[CH:21][CH:22]=3)=[CH:35][C:36]=2[CH2:41][O:40]1

참가 물질

5

반응물 2

HCID 218672176-{4-[3-(2,5-Dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonateHCID 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

생성물 1

HCID 693439983-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione수율 41.9%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6228Dimethylformamide용매

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온도
20 °C

실험 절차

A solution of 6-{4-[3-(2,5-dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonate (766 mg) in DMF (8 ml) was treated with tetrabutylammonium bromide (578 mg) and (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (544 mg) and the mixture was stirred at 20° C. for 3 d. The solvent was removed under reduced pressure, the residue was dissolved in CH2Cl2, washed with water and purified by chromatography on Biotage (40 g) eluting with 3% 2M NH3 in MeOH:CH2Cl2 to give the title compound (417 mg). ES+ve 554 (MH)+.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. custompurified by chromatography on Biotage (40 g)
  5. washeluting with 3% 2M NH3 in MeOH

출처 및 근거

ORD 기록
ord-fa08fb941b7f408493cdbe8dc12f1042
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144908B2

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